WO2011028320A2 - Dispersions of inorganic particulates containing alkoxycrylene - Google Patents
Dispersions of inorganic particulates containing alkoxycrylene Download PDFInfo
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- WO2011028320A2 WO2011028320A2 PCT/US2010/040869 US2010040869W WO2011028320A2 WO 2011028320 A2 WO2011028320 A2 WO 2011028320A2 US 2010040869 W US2010040869 W US 2010040869W WO 2011028320 A2 WO2011028320 A2 WO 2011028320A2
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- Prior art keywords
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- 239000006185 dispersion Substances 0.000 title claims description 116
- 239000000203 mixture Substances 0.000 claims abstract description 206
- 150000001875 compounds Chemical class 0.000 claims abstract description 103
- 239000011236 particulate material Substances 0.000 claims abstract description 60
- 238000000576 coating method Methods 0.000 claims abstract description 23
- 239000011248 coating agent Substances 0.000 claims abstract description 15
- 239000000463 material Substances 0.000 claims abstract description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000002270 dispersing agent Substances 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 78
- 239000000516 sunscreening agent Substances 0.000 claims description 75
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 74
- 230000000475 sunscreen effect Effects 0.000 claims description 74
- -1 alkoxy radical Chemical class 0.000 claims description 67
- 229910044991 metal oxide Inorganic materials 0.000 claims description 40
- 150000004706 metal oxides Chemical class 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 39
- 239000002245 particle Substances 0.000 claims description 37
- 239000011787 zinc oxide Substances 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 36
- 239000004408 titanium dioxide Substances 0.000 claims description 36
- 239000004904 UV filter Substances 0.000 claims description 31
- 239000004480 active ingredient Substances 0.000 claims description 23
- 239000000126 substance Substances 0.000 claims description 22
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 17
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical class C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 claims description 17
- 229960005193 avobenzone Drugs 0.000 claims description 12
- YBGZDTIWKVFICR-JLHYYAGUSA-N Octyl 4-methoxycinnamic acid Chemical group CCCCC(CC)COC(=O)\C=C\C1=CC=C(OC)C=C1 YBGZDTIWKVFICR-JLHYYAGUSA-N 0.000 claims description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 11
- 230000005855 radiation Effects 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 150000003722 vitamin derivatives Chemical class 0.000 claims description 9
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 8
- 235000017471 coenzyme Q10 Nutrition 0.000 claims description 8
- 235000013870 dimethyl polysiloxane Nutrition 0.000 claims description 8
- 229960003921 octisalate Drugs 0.000 claims description 8
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 8
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims description 7
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 7
- UVCJGUGAGLDPAA-UHFFFAOYSA-N ensulizole Chemical compound N1C2=CC(S(=O)(=O)O)=CC=C2N=C1C1=CC=CC=C1 UVCJGUGAGLDPAA-UHFFFAOYSA-N 0.000 claims description 7
- 239000004615 ingredient Substances 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 150000003918 triazines Chemical class 0.000 claims description 7
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims description 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 6
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 6
- 150000001565 benzotriazoles Chemical class 0.000 claims description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 6
- 229910052748 manganese Inorganic materials 0.000 claims description 6
- 239000011572 manganese Substances 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 claims description 5
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 claims description 5
- 241000723346 Cinnamomum camphora Species 0.000 claims description 5
- 235000021355 Stearic acid Nutrition 0.000 claims description 5
- 239000012964 benzotriazole Substances 0.000 claims description 5
- 229960000846 camphor Drugs 0.000 claims description 5
- 229930008380 camphor Natural products 0.000 claims description 5
- 229960000655 ensulizole Drugs 0.000 claims description 5
- 239000004816 latex Substances 0.000 claims description 5
- 229920000126 latex Polymers 0.000 claims description 5
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 5
- FMJSMJQBSVNSBF-UHFFFAOYSA-N octocrylene Chemical group C=1C=CC=CC=1C(=C(C#N)C(=O)OCC(CC)CCCC)C1=CC=CC=C1 FMJSMJQBSVNSBF-UHFFFAOYSA-N 0.000 claims description 5
- 229960000601 octocrylene Drugs 0.000 claims description 5
- WCJLCOAEJIHPCW-UHFFFAOYSA-N octyl 2-hydroxybenzoate Chemical compound CCCCCCCCOC(=O)C1=CC=CC=C1O WCJLCOAEJIHPCW-UHFFFAOYSA-N 0.000 claims description 5
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 claims description 4
- TYYHDKOVFSVWON-UHFFFAOYSA-N 2-butyl-2-methoxy-1,3-diphenylpropane-1,3-dione Chemical group C=1C=CC=CC=1C(=O)C(OC)(CCCC)C(=O)C1=CC=CC=C1 TYYHDKOVFSVWON-UHFFFAOYSA-N 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- ACTIUHUUMQJHFO-UHFFFAOYSA-N Coenzym Q10 Natural products COC1=C(OC)C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UHFFFAOYSA-N 0.000 claims description 4
- 229930003427 Vitamin E Natural products 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 229960004050 aminobenzoic acid Drugs 0.000 claims description 4
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 4
- 235000021466 carotenoid Nutrition 0.000 claims description 4
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 claims description 4
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 4
- WMWXXXSCZVGQAR-UHFFFAOYSA-N dialuminum;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3] WMWXXXSCZVGQAR-UHFFFAOYSA-N 0.000 claims description 4
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 claims description 4
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 4
- 229920005862 polyol Polymers 0.000 claims description 4
- 150000003077 polyols Chemical class 0.000 claims description 4
- 229920001296 polysiloxane Polymers 0.000 claims description 4
- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- 239000008117 stearic acid Substances 0.000 claims description 4
- 229940088594 vitamin Drugs 0.000 claims description 4
- 229930003231 vitamin Natural products 0.000 claims description 4
- 235000013343 vitamin Nutrition 0.000 claims description 4
- 239000011782 vitamin Substances 0.000 claims description 4
- 235000019165 vitamin E Nutrition 0.000 claims description 4
- 229940046009 vitamin E Drugs 0.000 claims description 4
- 239000011709 vitamin E Substances 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 claims description 3
- XPKVYKWWLONHDF-UHFFFAOYSA-N 2,3-dihydroxy-3-(2-hydroxyphenyl)prop-2-enoic acid Chemical compound OC(=O)C(O)=C(O)C1=CC=CC=C1O XPKVYKWWLONHDF-UHFFFAOYSA-N 0.000 claims description 3
- DRBARRGCABOUIE-UHFFFAOYSA-N 2,3-dihydroxy-3-phenylprop-2-enoic acid Chemical compound OC(=O)C(O)=C(O)C1=CC=CC=C1 DRBARRGCABOUIE-UHFFFAOYSA-N 0.000 claims description 3
- MOMKYJPSVWEWPM-UHFFFAOYSA-N 4-(chloromethyl)-2-(4-methylphenyl)-1,3-thiazole Chemical compound C1=CC(C)=CC=C1C1=NC(CCl)=CS1 MOMKYJPSVWEWPM-UHFFFAOYSA-N 0.000 claims description 3
- 229910052684 Cerium Inorganic materials 0.000 claims description 3
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 claims description 3
- 239000001263 FEMA 3042 Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000005639 Lauric acid Substances 0.000 claims description 3
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 claims description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical class C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 claims description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 claims description 3
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 3
- 239000000783 alginic acid Substances 0.000 claims description 3
- 229920000615 alginic acid Polymers 0.000 claims description 3
- 235000010443 alginic acid Nutrition 0.000 claims description 3
- 229960001126 alginic acid Drugs 0.000 claims description 3
- 150000004781 alginic acids Chemical class 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 3
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 claims description 3
- 229940063655 aluminum stearate Drugs 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 235000001014 amino acid Nutrition 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 3
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 claims description 3
- XVAMCHGMPYWHNL-UHFFFAOYSA-N bemotrizinol Chemical compound OC1=CC(OCC(CC)CCCC)=CC=C1C1=NC(C=2C=CC(OC)=CC=2)=NC(C=2C(=CC(OCC(CC)CCCC)=CC=2)O)=N1 XVAMCHGMPYWHNL-UHFFFAOYSA-N 0.000 claims description 3
- 229940110767 coenzyme Q10 Drugs 0.000 claims description 3
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 claims description 3
- HEAHZSUCFKFERC-UHFFFAOYSA-N ecamsule Chemical compound CC1(C)C2CCC1(CS(O)(=O)=O)C(=O)C2=CC(C=C1)=CC=C1C=C1C(=O)C2(CS(O)(=O)=O)CCC1C2(C)C HEAHZSUCFKFERC-UHFFFAOYSA-N 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 235000019136 lipoic acid Nutrition 0.000 claims description 3
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 3
- 239000012860 organic pigment Substances 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 150000003248 quinolines Chemical class 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- 235000012239 silicon dioxide Nutrition 0.000 claims description 3
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 claims description 3
- 235000019982 sodium hexametaphosphate Nutrition 0.000 claims description 3
- 235000019983 sodium metaphosphate Nutrition 0.000 claims description 3
- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 claims description 3
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- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 claims description 3
- 229960002663 thioctic acid Drugs 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
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- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 claims description 3
- 150000007968 uric acids Chemical class 0.000 claims description 3
- 235000019155 vitamin A Nutrition 0.000 claims description 3
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- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 2
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims description 2
- SNPLKNRPJHDVJA-ZETCQYMHSA-N D-panthenol Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCCO SNPLKNRPJHDVJA-ZETCQYMHSA-N 0.000 claims description 2
- 241000208690 Hamamelis Species 0.000 claims description 2
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 claims description 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 2
- UBNYRXMKIIGMKK-RMKNXTFCSA-N amiloxate Chemical compound COC1=CC=C(\C=C\C(=O)OCCC(C)C)C=C1 UBNYRXMKIIGMKK-RMKNXTFCSA-N 0.000 claims description 2
- 235000010323 ascorbic acid Nutrition 0.000 claims description 2
- 229960005070 ascorbic acid Drugs 0.000 claims description 2
- 239000011668 ascorbic acid Substances 0.000 claims description 2
- 150000008366 benzophenones Chemical class 0.000 claims description 2
- 229960002685 biotin Drugs 0.000 claims description 2
- 235000020958 biotin Nutrition 0.000 claims description 2
- 239000011616 biotin Substances 0.000 claims description 2
- 229960004203 carnitine Drugs 0.000 claims description 2
- 235000013985 cinnamic acid Nutrition 0.000 claims description 2
- 229930016911 cinnamic acid Natural products 0.000 claims description 2
- 235000001671 coumarin Nutrition 0.000 claims description 2
- 229960000956 coumarin Drugs 0.000 claims description 2
- SIUKXCMDYPYCLH-UHFFFAOYSA-N dihydroxycinnamic acid Natural products OC(=O)C=CC1=CC=CC(O)=C1O SIUKXCMDYPYCLH-UHFFFAOYSA-N 0.000 claims description 2
- 229960000304 folic acid Drugs 0.000 claims description 2
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- 239000011724 folic acid Substances 0.000 claims description 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 2
- 229960003966 nicotinamide Drugs 0.000 claims description 2
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- 239000010954 inorganic particle Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- VKPSKYDESGTTFR-UHFFFAOYSA-N isododecane Natural products CC(C)(C)CC(C)CC(C)(C)C VKPSKYDESGTTFR-UHFFFAOYSA-N 0.000 description 1
- 229940100554 isononyl isononanoate Drugs 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
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- CSSYQJWUGATIHM-IKGCZBKSSA-N l-phenylalanyl-l-lysyl-l-cysteinyl-l-arginyl-l-arginyl-l-tryptophyl-l-glutaminyl-l-tryptophyl-l-arginyl-l-methionyl-l-lysyl-l-lysyl-l-leucylglycyl-l-alanyl-l-prolyl-l-seryl-l-isoleucyl-l-threonyl-l-cysteinyl-l-valyl-l-arginyl-l-arginyl-l-alanyl-l-phenylal Chemical compound C([C@H](N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)C1=CC=CC=C1 CSSYQJWUGATIHM-IKGCZBKSSA-N 0.000 description 1
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- 235000012661 lycopene Nutrition 0.000 description 1
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- 235000011090 malic acid Nutrition 0.000 description 1
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- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
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- ZLQJVGSVJRBUNL-UHFFFAOYSA-N methylumbelliferone Natural products C1=C(O)C=C2OC(=O)C(C)=CC2=C1 ZLQJVGSVJRBUNL-UHFFFAOYSA-N 0.000 description 1
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- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
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- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 230000036542 oxidative stress Effects 0.000 description 1
- 229960002638 padimate o Drugs 0.000 description 1
- 229940098695 palmitic acid Drugs 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 229940088608 peg-9 polydimethylsiloxyethyl dimethicone Drugs 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 230000000176 photostabilization Effects 0.000 description 1
- 235000002949 phytic acid Nutrition 0.000 description 1
- 239000000467 phytic acid Substances 0.000 description 1
- 229940068041 phytic acid Drugs 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 229960002662 propylthiouracil Drugs 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
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- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000002207 retinal effect Effects 0.000 description 1
- IKGXIBQEEMLURG-BKUODXTLSA-N rutin Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@@H]1OC[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-BKUODXTLSA-N 0.000 description 1
- 229960004555 rutoside Drugs 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229960002718 selenomethionine Drugs 0.000 description 1
- 230000037307 sensitive skin Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 230000009759 skin aging Effects 0.000 description 1
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- 159000000000 sodium salts Chemical class 0.000 description 1
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- 239000003381 stabilizer Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- ARCJQKUWGAZPFX-UHFFFAOYSA-N stilbene oxide Chemical compound O1C(C=2C=CC=CC=2)C1C1=CC=CC=C1 ARCJQKUWGAZPFX-UHFFFAOYSA-N 0.000 description 1
- 150000001629 stilbenes Chemical class 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
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- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 125000005555 sulfoximide group Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000003655 tactile properties Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229940094937 thioredoxin Drugs 0.000 description 1
- 108060008226 thioredoxin Proteins 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 229940042585 tocopherol acetate Drugs 0.000 description 1
- 125000002640 tocopherol group Chemical class 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 229940025703 topical product Drugs 0.000 description 1
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 1
- ZCIHMQAPACOQHT-ZGMPDRQDSA-N trans-isorenieratene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/c1c(C)ccc(C)c1C)C=CC=C(/C)C=Cc2c(C)ccc(C)c2C ZCIHMQAPACOQHT-ZGMPDRQDSA-N 0.000 description 1
- LOIYMIARKYCTBW-OWOJBTEDSA-N trans-urocanic acid Chemical compound OC(=O)\C=C\C1=CNC=N1 LOIYMIARKYCTBW-OWOJBTEDSA-N 0.000 description 1
- LOIYMIARKYCTBW-UHFFFAOYSA-N trans-urocanic acid Natural products OC(=O)C=CC1=CNC=N1 LOIYMIARKYCTBW-UHFFFAOYSA-N 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 description 1
- SCRSFLUHMDMRFP-UHFFFAOYSA-N trimethyl-(methyl-octyl-trimethylsilyloxysilyl)oxysilane Chemical compound CCCCCCCC[Si](C)(O[Si](C)(C)C)O[Si](C)(C)C SCRSFLUHMDMRFP-UHFFFAOYSA-N 0.000 description 1
- UEVAMYPIMMOEFW-UHFFFAOYSA-N trolamine salicylate Chemical compound OCCN(CCO)CCO.OC(=O)C1=CC=CC=C1O UEVAMYPIMMOEFW-UHFFFAOYSA-N 0.000 description 1
- 229940030300 trolamine salicylate Drugs 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 229940040064 ubiquinol Drugs 0.000 description 1
- QNTNKSLOFHEFPK-UPTCCGCDSA-N ubiquinol-10 Chemical compound COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC QNTNKSLOFHEFPK-UPTCCGCDSA-N 0.000 description 1
- 229940035936 ubiquinone Drugs 0.000 description 1
- ORHBXUUXSCNDEV-UHFFFAOYSA-N umbelliferone Chemical compound C1=CC(=O)OC2=CC(O)=CC=C21 ORHBXUUXSCNDEV-UHFFFAOYSA-N 0.000 description 1
- HFTAFOQKODTIJY-UHFFFAOYSA-N umbelliferone Natural products Cc1cc2C=CC(=O)Oc2cc1OCC=CC(C)(C)O HFTAFOQKODTIJY-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 150000003712 vitamin E derivatives Chemical class 0.000 description 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
Definitions
- the present invention is directed to dispersions comprising particulate materials, preferably inorganic particulate materials in an alkoxycrylene carrier, and compositions, preferably sunscreen or dermatological formulations, comprising said dispersions. More particularly, the present invention is directed to sunscreen or dermatological formulations comprising dispersions of zinc oxide or titanium dioxide using an alkoxycrylene compound as the carrier.
- a sunscreen composition is a topical product comprising one or more UV filter compounds that absorb, scatter, and/or reflect some of the sun " s ultraviolet radiation on the skin when it is exposed to sunlight.
- the UV filter compound(s) can be classified into three groups: chromophore-containing organic compounds such as para-aminobenzoic acid (PABA), organic particulates such as such as methylene bis-benzotriazolyl
- T1NOSORB M by CIBA® tetramethylbutylphenol
- inorganic particulates such as kaolin, talc, and metal oxides (e.g. zinc oxide, titanium dioxide).
- Inorganic particulates are physical-barrier UV filters that reflect both UV-A and UV-B rays. Inorganic particulates offer the broadest protection against UV rays (i.e. below 290 nm to around 380 nm) that no single organic UV absorber can match. In addition, inorganic particulates provide high sun protection factors (SPFs), are economical to use, are completely stable on exposure to sunlight if properly treated, and do not cause skin problems because they are not absorbed into the skin. [0005] As shown in this assignee's pending applications, Serial Nos.
- alkoxy substituted a- cyano- ⁇ , ⁇ -diphenylacrylates alkoxycrylenes
- melhoxycrylenes return chromophore-containing UV filter agents, particularly butyl methoxydibenzoylmethane (Avobenzone), octyl methoxycinnamate (Octinoxate), and octyl salicylate (Octisalate)
- alkoxy substituted a- cyano- ⁇ , ⁇ -diphenylacrylates alkoxycrylenes
- melhoxycrylenes return chromophore-containing UV filter agents, particularly butyl methoxydibenzoylmethane (Avobenzone), octyl methoxycinnamate (Octinoxate), and octyl salicylate (Octisalate)
- Chromophore-containing UV filter agents work by absorbing ultraviolet light.
- the absorption of ultraviolet light by a chromophore-containing organic molecule causes the excitation of an electron in the chromophore moiety from an initially occupied, low energy orbital to a higher energy, previously unoccupied orbital.
- the energy of an absorbed photon is used to energize an electron and cause it to "jump" to a higher energy orbital, see Turro, Modern Molecular Photochemistry, 1991.
- Two excited electronic states derive from the electronic orbital configuration produced by UV light absorption. In one state, the electron spins are paired (antiparallel) and in the other state the electron spins are unpaired (parallel).
- the state with paired spins has no resultant spin magnetic moment, but the state with unpaired spins possesses a net spin magnetic moment.
- a state with paired spins remains a single state in the presence of a magnetic field, and is termed a singlet state.
- a state with unpaired spins interacts with a magnetic field and splits into three quantized states, and is termed a triplet state.
- the chromophore-containing organic molecule In the electronically excited state, the chromophore-containing organic molecule is prone to degrade via a number of known pathways and, therefore, can absorb little or no additional UV light, see Bonda, Cosmetics & Toiletries 123(2): 1 - 1 1 , (2008).
- R 1 and R. 2 is a straight or branched chain C 1 -C 30 alkoxy radical, preferably C 1 -C 8 , more preferably methoxy, and the non-alkoxy radical R ⁇ or R 2 is hydrogen; and R;, is a straight or branched chain C 1 -C 30 alkyl radical, preferably C2-C20.
- Ranges may be expressed herein as from “about” or “approximately” one particular value and/or to “about” or “approximately” another particular value. When such a range is expressed, another embodiment includes from the one particular value and/or to the other particular value. Similarly, when values are expressed as approximations, by use of the antecedent "about.” it will be understood that the particular value forms another embodiment.
- alkoxy herein refers to a radical extending from the para position of one or both of the phenyl rings having the formula O-R, wherein R is an alkyl radical, straight chain or branched having 1 to 30 carbon atoms, preferably wherein R is C 1 to C 8 , more preferably C 2 -C 20 , and most preferably -O-CH 3 (methoxy).
- R is an alkyl radical, straight chain or branched having 1 to 30 carbon atoms, preferably wherein R is C 1 to C 8 , more preferably C 2 -C 20 , and most preferably -O-CH 3 (methoxy).
- the oxygen atom of the alkoxy radical is covalently bonded to the para carbon atom of one of the phenyl rings, preferably having the formula (II or (III):
- R 3 is as previously defined.
- crylene refers to a chromophoric moiety that includes an a-cyano- ⁇ , ⁇ -diphenyl propanoic acid ester.
- cyano refers to a -C ⁇ N group, also designated "-CN.”
- the dispersions described herein comprise a combination of an inorganic particulate material, particularly a metal oxide, and a carrier for the inorganic particulate material comprising a compound of formula (I).
- the carrier for the inorganic particulate material can further comprise one or more additional carriers.
- the dispersions described herein can further comprise one or more additional particulate materials such as latex particles and/or organic pigments.
- the dispersions described herein can also be formulated to further comprise one or more coating materials for the inorganic particulate material and/or one or more dispersing agents for the inorganic particulate material.
- the dispersions described herein can optionally be combined with one or more UV-A photoactive compounds and/or one or more UV-B photoactive compounds.
- the photoactive compounds can be
- photodegradable compounds that reach an electronic singlet excited state upon exposure to UV radiation.
- photoactive compounds that can be combined with the dispersions described herein include dibenzoylmethane derivatives (e.g. Avobenzone), octyl methoxycinnamate (octinoxate), and octyl salicylate (octisalate), particularly a combination thereof.
- the dispersions described herein can also optionally be combined with one or more photostabilizing compounds such as oxybenzone, octocrylene, methylbenzilydene camphor, and naphthalene dicarboxylate esters.
- the dispersions described herein can also optionally be combined with a water soluble UV filter compound, such as sulfonated UV filters, and /or a hydroxybenzophenone compound.
- the dispersions described herein can also optionally be combined with a benzotriazole compound such as 2,2'-methylenebis(6-(2H-benzotriazol-2- yl)-4-(l ,l ,3,3-tetramethylbutyl)phenol) (Tinsosorb®), and/or a triazine compound.
- the dispersions described herein can further optionally be combined with one or more of the following: antioxidants (e.g. vitamin E derivatives, vitamin A derivatives), natural active ingredients (e.g.
- hydrophilic skin care ingredients e.g. water-soluble antioxidants, vitamins
- lipophilic active ingredients e.g. ubiquinones, retinoids, and carotinoids
- UV-sensitive active ingredients e.g. ubiquinones, retinoids, and carotinoids
- Dispersions comprising inorganic particulates are excellent sunscreen agents because they offer a broad range of protection from both UV-A and UV-B rays.
- inorganic particulates exist as particle aggregates (i.e. two or more crystals that have bonded irreversibly together during the manufacture process) instead of as individual crystals.
- groups of the particle aggregates often stick together to form agglomerates. Agglomerates, which act like individual large particles, are less transparent than aggregates, causing undesired whitening when applied to the skin, and reflect UV rays less efficiently than the same mass of smaller particles.
- inorganic particulates can provide their manufacturing process to prevent significant formation of agglomerates.
- zinc oxide a widely used inorganic particulate in sunscreen and dermatological formulations, has been found to be the most effective when its particles are manufactured to be less than 0.2 micrometers across.
- Zinc oxide particles in the range of 0.1 to 0.2 micrometers provide the best combination of attenuation and aesthetics because they are fine enough to appear almost completely transparent, yet effective across the full UV spectrum.
- the method comprises the steps of mixing the photoactive compound with a compound of formula (I) and exposing the mixture to UV radiation in an amount sufficient for the photoactive compound to reach an electronic singlet excited state.
- the compound of formula (I) accepts the singlet excited state energy from the excited photoactive compound, allowing the photoactive compound to return to its ground state so that it is capable of absorbing additional UV radiation before undergoing a photochemical reaction destructive to its UV-absorbing capability.
- the singlet excited state energy from the photon-excited photoactive compound is quenched through transfer from the photon-excited photoactive compound to the compound of formula (I), thereby photostabilizing the photoactive compound.
- sunscreen formulations comprising the metal oxide dispersions described herein comprising 3.4% or 1.7% by weight of an alkoxycrylene compound of formula (I), based on the total weight of the sunscreen formulation, have SPF values of 17 and 10, respectively.
- an alkoxycrylene compound of formula (I) is used as a carrier in a dispersion comprising a particulate material, preferably a UV filter substance
- and Ro is a straight or branched chain C 1 -C 30 alkoxy radical, preferably C 1 - C 8 , more preferably methoxy, and the non-alkoxy radical R 1 or R 2 is hydrogen; and R is a straight or branched chain alkyl radical, preferably
- the carrier makes up the bulk of the non-particulate UV filter substance in a dispersion.
- the carrier is dermatologically suitable (i.e. does not cause or promote adverse reactions upon the skin).
- Compounds that commonly function as carriers include silicones, synthetics esters and oils, natural esters and oils, and hydrocarbons.
- Some suitable carriers include vegetable oils, for example, fatty acid glycerides. fatty acid esters, and fatty alcohols. Specific examples include cyclopentasiloxane, eapric/caprylic triglycerides, isononyl isononanoate, Simmondsia chinensis (Jojoba) seed oil, Heikinthus annus
- the carrier is an alkoxycrylene compound of formula (I) and may or may not include one or more additional carriers, such as those identified above. In one specific embodiment of the invention, the carrier is a methoxycrylene compound.
- the carrier is ethylhexyl methoxycrylene (EHMC, SOLASTAYTM S, ).
- the alkoxycrylene carrier is combined with one or more additional carriers such as a C 12-C 15 alkylbenzoate and/or butyloctyl salicylate.
- the amount of the alkoxycrylene carrier need only be sufficient to provide a uniform dispersion of the inorganic particles when they are applied to the skin to ensure adequate coverage of the skin with the UV filter material.
- the alkoxycrylene carrier is present in the dispersion in an amount in the weight range of about 1 % to about 70% by weight, based on the total weight of the dispersion.
- the alkoxycrylene carrier is present in the dispersion in an amount in the weight range of about 10% to about 40% by weight, based on the total weight of the dispersion.
- the additional earner is present in an amount in the weight range of about 0% to about 35% by weight, preferably about 1 % to about 35% by weight, more preferably about 10% to about 25% by weight, based on the total weight of the dispersion.
- Preferred particulate UV filter substances for the purposes of the dispersion of the preferred embodiment are inorganic particulates, especially metal oxides and/or other metal compounds which are slightly soluble or insoluble in water, especially oxides of titanium (Ti0 2 ), zinc (ZnO), iron (e.g. Fe 2 0 3 ), zirconium (Zr0 2 ), silicon (Si0 2 ), manganese (e.g. MnO), aluminum (AI1O 3 ), cerium (e.g. Ce 2 0 3 ), mixed oxides of the corresponding metals, and mixtures of such oxides, and the sulfate of barium (BaSO.4).
- the metal oxides are preferably micronized (i.e. small particles having a particle size in the range of about 100 nm to about 370 nm.
- Zinc oxide particles and predispersions of zinc oxide particles which are suitable according to the invention are distinguished by a primary particle size of ⁇ 300 nm and can be obtained under the following proprietary names from the stated companies:
- Particularly preferred zinc oxides for the purposes of the invention are Z-Cote HP1 and Z-Cote from BASF and zinc oxide NDM from Haarmann & Reimer.
- Zinc oxides and other metal oxides are chemically and catalytically reactive.
- These metal oxide particles may advantageously be surface-treated ("coated"), the intention being, for example, to form or retain a hydrophilic, amphiphilic or hydrophobic character, and to reduce the reactivity and/or catalytic activity of the metal oxide.
- This surface treatment may consist of coating the particles by processes known per se with a thin hydrophilic and/or hydrophobic inorganic and/or organic layer.
- the various surface coatings may also contain water.
- Inorganic surface coatings for the purposes of the present invention may consist of oxides or hydrous oxides such as, for example, aluminum oxide (AI2O3), aluminum hydroxide Al(OH);, or aluminum oxide hydrate (also: alumina, CAS No.: 1333-84-2), sodium hexametaphosphate (NaP0 ) 6 , sodium metaphosphate (NaPO . i),,, silicon dioxide (Si0 2 ) (also: silica, CAS No.: 763 1-86-9) or iron oxide
- oxides or hydrous oxides such as, for example, aluminum oxide (AI2O3), aluminum hydroxide Al(OH);, or aluminum oxide hydrate (also: alumina, CAS No.: 1333-84-2), sodium hexametaphosphate (NaP0 ) 6 , sodium metaphosphate (NaPO . i),,, silicon dioxide (Si0 2 ) (also: silica, CAS No.: 763 1-86-9) or iron oxide
- Organic surface coatings for the metal oxide particles of the dispersions described herein may consist of polyols, amines or alkanolamines, vegetable or animal aluminum stearate, vegetable or animal stearic acid, lauric acid, dimethylpolysiloxane (also; dimethicones), methylpolysiloxane (methicones), simethicones (a mixture of
- These organic and organosilane surface coatings may occur alone, in combination and/or in combination with inorganic coating materials.
- the coatings usually comprise about 0 wt% to about 10 wt%, preferably about 1 wt% to about 10 wt%, based on the total weight of the compositions described herein.
- silane surface coatings such as triethoxycaprylylsilane.
- Suitable silane coatings for the purposes of the present invention are obtainable under the following proprietary names from Kobo
- Titanium dioxide particles when incorporated into the dispersions described herein, may be in the form of both the rutile and anatase crystal modification and may
- Coated and uncoated titanium dioxides may be used in the form of commercially available oily or aqueous predispersions. It may be advantageous to add dispersion aids and/or solubilization mediators, together with the T1O2 and alkoxycrylene dispersions described herein, in typical amounts of about 0 wt% to about 10 wt%, preferably about 1 wt% to about 3 wt , based on the total weight of the composition.
- Suitable titanium dioxide particles and predispersions of titanium dioxide particles for the dispersions described herein are obtainable under the following proprietary names from the stated companies:
- the titanium dioxides of the preferred dispersions described herein are distinguished by a primary particle size between about 10 nm to about 150 nm.
- Titanium dioxide particles particularly preferred for the purposes of the dispersions described herein are MT- 100 Z and MT-100 TV from Tayca Corporation, Eusolex T-2000 from Merck and titanium dioxide T 805 from Degussa.
- the titanium dioxide particles of the dispersion are uncoated and doped with low levels of manganese, e.g. about 0.1 wt% to about 5 wt%, preferably 0.3 wt% to about 1 wt% (e.g. 0.67 wt%), based on the total weight of the Ti0 2 particles, after doping.
- low-level inclusion of manganese or some other transition metal ions into T1O 2 particles introduces extra energy levels into the titanium dioxide, which are present in the UVA portion of the ultraviolet spectrum.
- the uncoated manganese-doped titanium dioxide particles deliver a broad spectrum of UV-A and UV-B protection, act as free radical scavengers, enhance the photostability of other UV active compounds in the resulting formulation, and help to avoid whitening on skin.
- the coated metal oxides of another embodiment may also be used in various combinations with other coated or uncoated metal oxides, for example coated zinc oxide with coated or uncoated titanium dioxide particles. Such combinations may be provided in any selected weight ratio of coated/coated or coated/uncoated metal oxide in the range of 1 : 10 to 10: 1 , for example.
- Latex particles are other advantageous particles that can be included in the dispersions described herein. Latex particles which are particularly advantageous are described in the following publications: U.S. Pat. No. 5,663,213 and EP 0 761 201.
- Particular advantageous latex particles are those formed from water and styrene/acrylate copolymers and available for example under the proprietary name "Alliance SunSphere" from Rohm & Haas.
- An advantageous organic pigment 2,2'-methylenebis(6-(2H-benzotriazol-2-yl)-4- ( 1, 1 ,3,3-tetramethylbutyl- )phenol) (INCI: bis-octyltriazol), which is obtainable under the proprietary name Tinosorb ® M from CIBA-Chemikalien GmbH, can also be included in one embodiment of the dispersions described herein.
- the dispersions may further comprise a dispersant in typical amounts of about 0 wt% to about 10 wt%, preferably about 1 wt% to about 5 wt%, based on the total weight of the dispersion.
- Dispersants are used to "wet" the particles so that they disperse in the earner more easily and remain dispersed over time, or to act as emulsifiers that aid in the incorporation of the dispersion in the finished formulation.
- examples of dispersants include polyesters or salts of one or more hydroxycarboxyiic acids, monoesters of fatty acid alkanolamides (e.g.
- ethanolamine propanolamine, or aminoethyl ethanolamine
- carboxylic acids and their salts based on 6-22 carbon unsaturated fatty acids phosphate esters, neutralized phosphoric acids, stearic acids such as hydroxystearic acid, lecithin, polymers or copolymers of acrylic or methacrylic acids, ethoxy compounds (e.g. ethoxylated phosphate esters), hyperdispersants (e.g.
- the metal oxide is present in an amount in the weight range of about 10% to about 70% by weight, based on the total weight of the dispersion.
- the metal oxide is present in an amount in the weight range of about 20% to about 65% by weight, based on the total weight of the dispersion. In another embodiment, the metal oxide is present in an amount in the weight range of about 40% to about 60% by weight, based on the total weight of the dispersion.
- the metal oxide particulate dispersion comprising the alkoxycrylene compound of formula (I) as the carrier is combined in a sunscreen or dermatological formulation.
- a sunscreen or dermatological formulation generally includes UV-A and UV-B photoactive compounds in a cosmetically acceptable carrier, optionally including additives, such as emollients, stabilizers, emulsifiers, and combinations thereof. These additives can be used in preparing a UV filter composition in an emulsion (oil-in-water or water-in-oil) from a composition that includes one or more photoactive compounds and a solvent or a solvent combination that includes one or more organic solvents and water.
- the emulsion is an oil-in-water emulsion, wherein the oil phase is primarily formed from a mixture of an organic and/or inorganic UV filter compound(s) and one or more organic solvents.
- the sunscreen or dermatological formulation comprises the metal oxide particulate in an amount in the weight range of about 0.1 wt% to about 25 wt% and the alkoxycrylene compound of formula (I) in an amount in the weight range of about 0.1 wt% to about 15 wt%, based on the total weight of the formulation.
- the sunscreen or dermatological formulation comprises the metal oxide particulate in an amount in the weight range of about 2 wt% to about 8 wt% and the alkoxycrylene compound of formula (I) in an amount in the weight range of about 1 wt% to about 7 wt%, based on the total weight of the formulation.
- the sunscreen or dermatological formulation comprises the metal oxide particulate in an amount in the weight range of about 3 wt% to about 7 wt% and the alkoxycrylene compound of formula (I) in an amount in the weight range of about 2 wt% to about 5 wt%, based on the total weight of the formulation.
- the sunscreen or dermatological formulation comprising the dispersion of the invention can further comprise additional photoactive compound(s), wherein the photoactive compound(s) act to absorb UV radiation and thereby protect the substrate (e.g., human skin, resins, films, and the like) from the harmful effects of UV radiation.
- the absorption process causes a photoactive compound to reach an excited state, wherein the excited state is characterized by the presence of excited electronic energy (e.g., singlet state energy or triplet state energy), as compared to the ground state of the photoactive compound.
- excited electronic energy e.g., singlet state energy or triplet state energy
- the alkoxycrylene molecules described herein accept electronic singlet excited state energy from UV-absorbers, particularly Avobenzone, octyl methoxycinnamate (octinoxate), and octyl salicylate (octisalate).
- the alkoxycrylenes also are very effective UVA absorbers in addition to providing electronic singlet state energy quenching of other UV-absorbing compounds in sunscreen compositions.
- the alkoxycrylene molecules described herein are especially effective when combined with one or more additional electronic singlet excited state quenching compounds such as oxybenzone.
- Particularly surprising photostabilization is achieved in sunscreen or dermatological formulations containing octyl methoxycinnamate and Avobenzone together with the dispersions of the invention comprising the alkoxycrylene molecules described herein.
- a photoactive compound is one that responds to light photoelectrically.
- the sunscreen or dermatological formulations described herein and, in another embodiment, the dispersions described herein containing a metal oxide particulate material together with the carrier of formula (I), described in this assignee's pending applications, Serial Nos.
- the alkoxycrylenes are useful photostabilizers and/or photoactive compounds in the dispersions described herein when combined with any single or combination of organic photoactive compounds identified in Shaath, Nadim, Encyclopedia of UV filters, ⁇ 2007, hereby incorporated by reference. Photostability is a problem with all organic UV filters because they all reach an electronic singlet excited state upon exposure to UV radiation. [0044] It is theorized that all of the following UV fillers are photostabilized by the dispersions described herein comprising inorganic particulates and the alkoxycrylene compounds of formula (I) as carriers, including each of the following, including
- p-aminobenzoic acid its salts and its derivatives (ethyl, isobutyl, glyceryl esters; p-dimethylaminobenzoic acid); anthranilates (o- aminobenzoates; methyl, menthyl, phenyl, benzyl, phenylethyl, linalyl, terpinyl, and cyclohexenyl esters); salicylates (octyl, amyl, phenyl, benzyl, menthyl (homosalate), glyceryl, and dipropyleneglycol esters); cinnamic acid derivatives (menthyl and benzyl esters, alpha-phenyl ciiinamonitrile; butyl cinnamoyl pyruvate); dihydroxycinnamic acid derivatives (umb
- hydroquinone and benzophenones (oxybenzone, sulisobenzone, dioxybenzone, benzoresorcinol, octabenzone, 4-isopropyldibenzoylmethane,
- UV filters should be particularly photostabilized by the dispersions described herein comprising inorganic particulates and the alkoxycrylene compounds of formula (I) as carriers: 2-ethylhexyl p-methoxycinnamate, 4,4'-t-butyl
- the sunscreen or dermatological formulations comprising the dispersions described herein can include a variety of photoactive compounds, preferably including one or more UV-A photoactive compounds and one or more UV-B photoactive compounds.
- a sunscreen or dermatological formulation comprising the dispersion includes a photoactive compound selected from the group consisting of p-aminobenzoic acid and salts and derivatives thereof; anthranilate and derivatives thereof; dibenzoylmethane and derivatives thereof; salicylate and derivatives thereof; cinnamic acid and derivatives thereof;
- dihydroxycinnamic acid and derivatives thereof camphor and salts and derivatives thereof; trihydroxycinnamic acid and derivatives thereof; dibenzalacetone naphtholsulfonate and salts and derivatives thereof; benzalacetophenone naphtholsulfonate and salts and derivatives thereof; dihydroxy-naphthoic acid and salts thereof; o-hydroxydiphenyldisulfonate and salts and derivatives thereof; p-hydroxydiphenyldisulfonate and salts and derivatives thereof; coumarin and derivatives thereof; diazole derivatives; quinine derivatives and salts thereof; quinoline derivatives; uric acid derivatives; vilouric acid derivatives; tannic acid and derivatives thereof; hydroquinone; diethylamino hydroxybenzoyl hexyl benzoate and salts and derivatives thereof; and combinations of the foregoing.
- the sunscreen or dermatological formulations comprising the dispersions described herein further include a dibenzoylmethane derivative, such as PARSOL 1789 (Avobenzone).
- a dibenzoylmethane derivative such as PARSOL 1789 (Avobenzone).
- UV A radiation (about 320 nm to about 400 nm), is recognized as contributing to causing damage to skin, particularly to very lightly colored or sensitive skin.
- a sunscreen or dermatological formulation comprising the dispersion of the invention disclosed herein preferably includes a UV-A photoactive compound.
- dermatological formulation comprising the dispersion of the invention disclosed herein includes a dibenzoylmethane derivative UV-A photoactive compound.
- dibenzoylmethane derivatives include, 2-methyldibenzoylmethane; 4- methyldibenzoylmethane; 4-isopropyldibenzoylmethane; 4-tert-butyldibenzoylmethane; 2,4- dimethyldibenzoylmethane; 2,5-dimethyldibenzoylmethane; 4,4'- diisopropyldibenzoylmethane; 4,4'-dimethoxydibenzoylmethane; 4-tert-butyl-4'- methoxydibenzoylmethane; 2-methyl-5-isopropyl-4'-methoxydibenzoylmethane; 2-methyl-5- tert-butyl-4'-methoxydibenzoylmethane; 2,4-dimethyl-4'-methoxydibenzoylmethane; 2,6- dimethyl-4-tert-butyl-4'-meth
- preferred cosmetically acceptable photoactive compounds and concentrations include: aminobenzoic acid (also called para aminobenzoic acid and PABA: 15% or less), Avobenzone (also called butyl methoxy dibenzoylmethane; 3% or less), cinoxate (also called 2 ethoxyethyl p methoxycinnamate; 3% or less), dioxybenzone (also called benzophenone 8; 3% or less), homosalate ((also called 3,3,5- trimethylcyclohexyl salicylate, 15% or less), , menthyl anthranilate (also called menthyl 2 aminobenzoate; 5% or less), octocrylene (also called 2 ethylhexyl 2 cyano 3,3
- diphenylacrylate 10% or less
- octyl methoxycinnamate 7.5% or less
- octyl salicylate also called 2 ethylhexyl salicylate; 5% or less
- oxybenzone also called benzophenone 3; 6% or less
- padimate O also called octyl dimethyl PABA; 8% or less
- phenylbenzimidazole sulfonic acid water soluble; 4% or less
- sulisobenzone also called benzophenone 4; 10% or less
- titanium dioxide (25% or less
- trolamine salicylate also called triethanol amine salicylate; 12% or less
- zinc oxide 25% or less
- compositions include diethanolamine methoxycinnamate ( 10% or less), ethyl- [bis(hydroxypropyl)] aminobenzoate (5% or less), glyceryl aminobenzoate (3% or less), 4 isopropyl dibenzoylmethane (5% or less), 4 methylbenzylidene camphor (6% or less), terephthalylidene dicamphor sulfonic acid (10% or less), and sulisobenzone (also called benzophenone 4, 10% or less).
- preferred cosmetically acceptable photoactive compounds and preferred concentrations include: PABA (5% or less), camphor
- benzalkonium methosulfate (6% or less), homosalate ( 10% or less), benzophenone 3 (10% or less), phenylbenzimidazole sulfonic acid (8% or less, expressed as acid), terephthalidene dicamphor sulfonic acid (10% or less, expressed as acid), butyl methoxydibenzoylmethane (5% or less), benzylidene camphor sulfonic acid (6% or less, expressed as acid), octocrylene ( 10% or less, expressed as acid), polyacrylamidomethyl benzylidene camphor (6% or less), ethylhexyl methoxycinnamate (10% or less), PEG 25 PABA ( 10% or less), isoamyl p methoxycinnamate ( 10% or less), ethylhexyl triazone (5% or less), drometrizole trielloxane ( 15% or less), diethylhexyl
- UV filters are commercially available.
- suitable commercially available organic UV filters are identified by trade name and supplier in Table 2 below:
- one or more of a highly polar solvent is present in the oil-phase of the formulation.
- a sufficient amount of a polar solvent is present in the sunscreen or dermatological compositions described herein to raise the dielectric constant of the oil-phase of the composition to a dielectric constant of at least about 7, preferably at least about 8.
- the alkoxycrylene molecules described herein yield unexpected photostability in comparison to other carriers.
- a photoactive compound can be considered stable when, for example, after 30 MED irradiation the photoactive compound has retained at least about 90% of its original absorbance at a wavelength, or over a range of wavelengths of interest (e.g., the wavelength at which a photoactive compound has a peak absorbance, such as 350-370 nm for
- a sunscreen or dermatological formulation comprising the dispersion of the invention can include a plurality of photoactive compounds and a sunscreen or dermatological formulation comprising the dispersion of the invention, as a whole, can be considered stable when, for example, after 30 MED irradiation the sunscreen composition has retained at least about 90% of its original absorbance at one or more wavelengths of interest (e.g., at or near the peak absorbance wavelength of the primary photoactive compound).
- the sunscreen or dermatological formulations including the dispersions described herein, also include a dibenzoylmethane derivative, such as PARSOL 1789 (Avobenzene) and/or a dialkyl naphthalate ester.
- a dibenzoylmethane derivative such as PARSOL 1789 (Avobenzene) and/or a dialkyl naphthalate ester.
- dibenzoylmethane derivatives particularly PARSOL 1789 (Avobenzone).
- dialkyl naphthalate esters for which R 1 and/or R ⁇ represent branched alkyl groups with 6 to 10 carbon atoms are advantageous, as described in U.S. Patent Nos. 5,993,789 and 6, 1 33,931, the disclosures of which are hereby incorporated by reference.
- Diethylhexyl naphthalate esters, as described in U.S. Patent Nos. 5,993,789 and 6,1 13,931 are very particularly preferred which are available, e.g., under the trade name Hallbrite TQTM from CP Hall or Corapan TQTM from H&R.
- the sunscreen or dermatological formulations described herein may advantageously contain from about 0.001% to about 30% by weight, preferably from about 0.01% to about 20% by weight, very particularly preferred from about 0.5% to about 15% by weight, of one or more dialkyl naphthalate esters, as described in U.S. Patent Nos. 5,993,789 and 6, 1 13,931.
- a sunscreen or dermatological formulation comprising a particulate material/formula (I) dispersion is combined with a water soluble UV filter compound and/or a broad-band filter compound and optionally, but preferably, together with a dibenzoylmethane derivative and/or a dialkyl naphthalate ester.
- Water-soluble UV filter substances that are advantageously included in the dispersions described herein, in another embodiment, are sulfonated UV filters, in particular: phenylene- l ,4-bis(2-benzimidazyl)-3,3'-5,5'-tetrasulfonic acid, which has the following structure:
- salts especially the corresponding sodium, potassium or triethanolammoniurn salts, in particular phenylene- 1 ,4-bis(2-benzimidazyl)- -3,3'-5,5'-tetrasulfonic acid bissodium salt
- sulfonated UV filters are the salts of 2-phenylbenzimidazole- 5-sulfonic acid, such as its sodium, potassium or its triethanolammoniurn salts, and the sulfonic acid itself
- water-soluble UV-B and/or broad-band filter substances for the purposes of this water-soluble UV filter-containing embodiment are, for example, sulfonic acid derivatives of 3-benzyIidenecamphor, such as, for example, 4-(2-oxo-3- bornylidenemethyl)benzene-sulfonic acid, 2-methyl-5-(2-oxo-3-bornylidenemethyl)sulfonic acid and the salts thereof.
- sulfonic acid derivatives of 3-benzyIidenecamphor such as, for example, 4-(2-oxo-3- bornylidenemethyl)benzene-sulfonic acid, 2-methyl-5-(2-oxo-3-bornylidenemethyl)sulfonic acid and the salts thereof.
- the total amount of one or more water-soluble UV filter substances in the sunscreen or dermatological formulations of this embodiment is advantageously chosen from the range of about 0.01% by weight to about 20% by weight, preferably from about 0.1 to about 10% by weight, in each case based on the total weight of the formulations.
- the sunscreen or dermatological formulation comprising dispersion is combined with a hydroxybenzophenone compound and/or a broad-band filter compound and optionally, but preferably, together with a dibenzoylmethane derivative and/or a dialkyl naphthalate ester.
- Hydroxybenzophenones are characterized by the following structural formula:
- R and R 2 independent of one another are hydrogen. or C 3 -C 10 -cyloalkenyl, wherein the substituents R 1 and R 2 together with the nitrogen atom to which they are bound can form a 5- or 6-ring and R 3 is a C radical.
- a particularly advantageous hydroxybenzophenone is the 2-(4'-diethyIamino-2'- hydroxybenzoyl)benzoic acid hexyl ester (also: aminobenzophenone) which is characterized by the following structure:
- sunscreen or dermatological formulations described herein contain from about 0.1% to about 20% by weight, advantageously from about 0.1 % to about 15% by weight, very particularly preferred from about 0.1% to about 10% by weight, of one or more hydroxybenzophenones.
- a sunscreen or dermatological formulation containing the particulate material/formula (I) dispersion is combined with a benzotriazole derivative compound and/or a broad-band filter compound and optionally, but preferably, together with a dibenzoylmethane derivative and/or a dialkyl naphthalate ester.
- UV filter substances selected from the group of benzotriazole derivatives
- the dispersions include a benzotriazole compound having a structural formula:
- R 1 and R 2 are, independently of one another, selected from the group of branched or unbranched C 1 -C 18 -alkyl radicals, of C 5 -C 12 -cycloalkyl or aryl radicals which are optionally substituted by one or more C 1 -C 4 alkyl groups.
- the preferred benzotriazole derivative is 2,2'-methylenebis(6-(2H-benzotriazol-2- yl)-4-( l ,l ,3,3-tetramethylbutyl)phenol), obtainable under the proprietary name Tinosorb 1® from CIBA-Chemikalien GmbH (INCl: bisoctyltriazole), which is characterized by the chemical structural formula:
- Another advantageous broadband filter that can be combined with the dispersion in this benzotriol-containing embodiment is 2-(2H-benzotriazol-2-yI)-4-methyl-6-[2-methyl-3- [ l,3,3,3-tetramethyl-l-[(t rimethyl-silyl)oxy
- propyl (phenol, in the finished cosmetic or dermatological composition is advantageously in the range from about 0.1 % to about 15.0% by weight, preferably from about 0.5% to about 10.0% by weight, based on the total weight of the compositions.
- the sunscreen or dermatological formulation containing the particulate material/formula (I) dispersion is combined with an asymmetrically substituted triazine derivative and/or a broad-band filter compound and optionally, but preferably, together with a dibenzoylmethane derivative and/or a dialkyl naphthalate ester to obtain an increased sun protection factor.
- Asymmetrically substituted triazine derivatives display a good light protection effect.
- Their main disadvantage is, however, that their solubility is low in conventional oil components.
- R is a branched or unbranched C i -C i g-alkyl radical, a Cs-C ⁇ -cycloalkyl radical, optionally substituted by one or more C) -C4-alkyl groups, and
- X is an oxygen atom or an NH group
- Ri is a branched or unbranched C t -C 1 8-alkyl radical, a Cs-C ⁇ -cycloalkyl radical, optionally substituted by one or more Ci-C4-alkyl groups, or a hydrogen atom, an alkali metal atom, an ammonium group or a group of the formula
- A is a branched or unbranched C i -Cig-alkyl radical, a Cs-C ⁇ -cycloalkyl or aryl radical, optionally substituted by one or more C
- R3 is a hydrogen atom or a methyl group, n is a number from 1 to 10,
- R 2 is a branched or unbranched Ci -Cia-alkyl radical, a C5-C
- R 2 is a branched or unbranched Ci-C
- A is a branched or unbranched C 1 -C 18 -alkyl radical, a Cs-Ci ⁇ -cycloalkyl or aryl radical, optionally substituted by one or more C 1 -C 4 -alkyl groups,
- R3 is a hydrogen atom or a methyl group, n is a number from 1 to 10, if X is an oxygen atom.
- the sunscreen or dermatologial formulations comprising the dispersions described herein include a content of least one asymmetrically substituted s-triazine selected from the group of
- bisresorcinyltriazines are advantageous for this embodiment.
- Particularly advantageous bisresorcinyltriazines comprise R 4 and R 5 selected from the group of branched or unbranched alkyl groups of 1 to 18 carbon atoms.
- the alkyl groups may also again advantageously be substituted by silyloxy groups.
- Ai is advantageously a substituted hornocyclic or heterocyclic aromatic five-membered ring or six-membered ring.
- R 6 is a hydrogen atom or a branched or unbranched alkyl group with 1 to 10 carbon atoms, in particular 2,4-bis ⁇ [4-(2-ethylhexyloxy)-2-hydroxy]phenyl ⁇ -6-(4-methoxyphenyl)- 1,3,5-triazine (INCI: aniso triazine), which is obtainable under the proprietary name
- Tinosorb ® S from CIBA-Chemikalien GmbH and is characterized by the following structure:
- the sunscreen or dermatological formulations comprising the dispersions described herein include an asymmetrically substituted s-triazine whose chemical structure is represented by the formula
- dioctylbutylamidotriazone (INCI) and is obtainable under the proprietary name UVASORB HEB from Sigma 3 V.
- the asymmetrically substituted s-triazine derivative(s) of the invention are advantageously, but optionally, incorporated into the oil phase of the sunscreen or dermatological formulation comprising the particulate material/formula (I) dispersions described herein.
- the total amount of one or more asymmetrically substituted s-triazine derivatives, in particular of dioctylbutylamidotriazone, in the sunscreen or dermatological formulation comprising the particulate material/formula (I) dispersions described herein is
- material/formula (I) dispersions described herein can be used for cosmetic or dermatological UV light-protection, and/or for the treatment, care and cleansing of the skin and/or hair and as a cosmetic product in decorative cosmetics.
- These compositions, with or without additional UV filter(s) and/or dispersing aids, and/or other additives are applied to the skin and or the hair in a sufficient quantity in the manner customary for cosmetics.
- material/formula (I) dispersions described herein can comprise cosmetic auxiliaries such as those conventionally used in such formulations, e.g. preservatives, bactericides, perfumes, antifoams, dyes, pigments which have a coloring effect, thickeners, moisturizers and/or humectants, fats, oils, waxes or other conventional constituents of a sunscreen or
- cosmetic auxiliaries such as those conventionally used in such formulations, e.g. preservatives, bactericides, perfumes, antifoams, dyes, pigments which have a coloring effect, thickeners, moisturizers and/or humectants, fats, oils, waxes or other conventional constituents of a sunscreen or
- dermatological formulation such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.
- one or more antioxidants may be added to the particulate material/formula (I) dispersions described herein. According to this embodiment, any antioxidant suitable or conventional for sunscreen or dermatological applications can be used.
- Particularly advantageous antioxidants are chosen from the group consisting of amino acids (e.g. glycine, histidine, tyrosine, tryptophan) and derivatives thereof, imidazoles (e.g. urocanic acid) and derivatives thereof, peptides such as D,L-camosine, D-carnosine, L- carnosine and derivatives thereof (e.g. anserine), carotenoids, carotenes (e.g. .alpha.-carotene, .beta. -carotene, lycopene) and derivatives thereof, chlorogenic acid and derivatives thereof, lipoic acid and derivatives thereof (e.g.
- amino acids e.g. glycine, histidine, tyrosine, tryptophan
- imidazoles e.g. urocanic acid
- peptides such as D,L-camosine, D-carnosine, L- carnosine and derivatives thereof (e.g
- thiols e.g. thioredoxin, glutathione, cysteine, cystine, cystamine and the glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, . gamma.
- sulfoximine compounds e.g. buthionine sulfoximines, homocysteine sulfoximine, buthionine sulfones, penta-, hexa-, heptathionine sulfoximine
- very low tolerated doses e.g.
- chelating agents e.g. .alpha. -hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin
- .alpha. -hydroxy acids e.g. citric acid, lactic acid, malic acid
- humic acid e.g. citric acid, lactic acid, malic acid
- bile acid e.g. citric acid, lactic acid, malic acid
- humic acid e.g. citric acid, lactic acid, malic acid
- bile extracts e.g. citric acid, lactic acid, malic acid
- humic acid e acid
- bile acid bile extracts
- bilirubin biliverdin
- EDTA EGTA
- unsaturated fatty acids and derivatives thereof e.g.
- .gamma.-linolenic acid linoleic acid, oleic acid
- folic acid and derivatives thereof ubiquinone and ubiquinol and derivatives thereof
- vitamin C and derivatives e.g. ascorbyl palmitate, Mg ascorbyl phosphate, ascorbyl acetate
- tocopherols and derivatives e.g.
- vitamin E acetate
- vitamin A and derivatives vitamin A palmitate
- coniferyl benzoate of gum benzoin rutinic acid and derivatives thereof, .alpha.-glycosylrutin, ferulic acid, furfurylideneglucitol, carnosine, butylhydroxytoluene, butylhydroxyanisole,
- nordihydroguaiaretic acid trihydroxybutyro-phenone, uric acid and derivatives thereof, mannose and derivatives thereof, zinc and derivatives thereof (e.g. ZnO, ZnS0 4 ), selenium and derivatives thereof (e.g. selenomethionine), stilbenes and derivatives thereof (e.g.
- stilbene oxide trans-stilbene oxide
- derivatives salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids
- the amount of antioxidants (one or more compounds) in the formulations is preferably from about 0.001% to about 30% by weight, particularly preferably from about 0.05% to about 20% by weight, in particular from about 0.1% to about 10% by weight, based on the total weight of the preparation.
- vitamin E and/or derivatives thereof are the antioxidant or antioxidants, it is advantageous to choose their respective concentrations from the range from about 0.001 % to about 10% by weight, based on the total weight of the formulation.
- vitamin A, vitamin A derivatives, carotenes, or carotene derivatives are the antioxidant or antioxidants, it is advantageous to choose their respective concentrations from the range from about 0.001% to about 10% by weight, based on the total weight of the formulation.
- the sunscreen or dermatological formulations comprising the comprising the particulate material/formula (1) dispersions described herein comprise further cosmetic or dermatological active ingredients, preferred active ingredients being antioxidants which can protect the skin against oxidative stress.
- compositions are natural active ingredients and/or derivatives thereof, such as e.g. ubiquinones, retinoids, carotenoids, creatine, taurine and/or ⁇ -alanine.
- material/formula (I) dispersions described herein which comprise e.g. known antiwrinkle active ingredients, such as flavone glycosides (in particular a-glycosylrutin), coenzyme Q10.
- vitamin E and/or derivatives and the like are particularly advantageously suitable for the prophylaxis and treatment of cosmetic or dermatological changes in skin, as arise, for example, during skin aging (such as, for example, dryness, roughness and formation of dryness wrinkles, itching, reduced refatting (e.g. after washing), visible vascular dilations (teleangiectases, couperosis), flaccidity and formation of wrinkles and lines, local
- hyperpigmentation, hypopigmentation and abnormal pigmentation e.g. age spots
- increased susceptibility to mechanical stress e.g. cracking
- they are advantageously suitable against the appearance of dry or rough skin.
- the sunscreen or dermatological formulation comprising the particulate material/formula (I) dispersions described herein may be combined with one or more hydrophilic skincare active ingredients and/or broad-band filter compounds and optionally, but preferably, together with a dibenzoylmethane derivative.
- biotin biotin ; carnitine and derivatives ; creatine and derivatives ; folic acid ; pyridoxine ;
- Particularly advantageous hydrophilic active ingredients for the purposes of this embodiment are also water-soluble antioxidants, such as, for example, vitamins.
- the amount of hydrophilic active ingredients (one or more compounds) in the formulations is preferably from about 0.0001 % to about 10% by weight, particularly preferably from about 0.001% to about 5% by weight, based on the total weight of the formulation.
- the sunscreen or dermatological formulation comprising the particulate material/f ormula (I) dispersions described herein are combined with a lipophilic oxidation or UV-sensitive active ingredients, such as retinoic acid and its derivatives, e.g., tretinoin or isotretinoin and/or a broad-band filter compound and optionally, but preferably, together with a dibenzoylmethane derivative.
- a lipophilic oxidation or UV-sensitive active ingredients such as retinoic acid and its derivatives, e.g., tretinoin or isotretinoin and/or a broad-band filter compound and optionally, but preferably, together with a dibenzoylmethane derivative.
- Advantageous lipophilic active ingredients which are stabilized in an excellent manner with the formula (I)- containing dispersions described herein are those whose log P value is greater than 3.5.
- P is the partition coefficient, which is defined as the ratio of the equilibrium concentration of a dissolved substance in a two-phase system which consists of two solvents which are essentially immiscible with one another. These two solvents are. in the present case, n-octanol and water, i.e.
- retinoid compounds vitamin A acid and/or derivatives thereof.
- the group of retinoids advantageous according to this embodiment of the invention is defined as including all cosmetically and/or pharmaceutically acceptable retinoids, including retinol and its esters, retinal and also retinoic acid (vitamin A acid) and esters thereof.
- retinol with a log P value of about 7
- retinyl palmitate with a log P value of about 13
- Further lipophilic acid ingredients advantageous according to this embodiment are carotenoids.
- ⁇ -carotene which has a log P value of 15, for example, is particularly advantageous.
- lipoic acid and derivatives are: lipoic acid and derivatives, vitamin E and derivatives, vitamin F, dioic acid [8-hexadecene- l , 16-dicarboxylic acid (CAS number 20701-68-2)1
- the amount of lipophilic active ingredients (one or more compounds) in the sunscreen or dermatological formulations described herein is preferably from about 0.0001 % to about 10% by weight, particularly preferably from about 0.001% to about 5% by weight, based on the total weight of the formulation.
- Zinc oxide dispersions using ethylhexyl methoxycrylene (SOLASTAYTM S,), butyloctyl salicylate (control), or CI 2- 15 alkyl benzoate (control) as carriers were supplied by either Dynamic Dispersions LLC “DO” or Kobo Products “Kobo” and formulated as shown in Table 3.
- the zinc oxide particles (Z-Cote HPl) comprise a 2% dimethicone coating and were supplied by BASF.
- Sunscreens were formulated comprising 10% to 13.3% of the zinc oxide dispersions of Table 3 and the SPF and UV A-PF values were determined as shown in Table 4.
- Control sunscreen formulations comprising dispersions of zinc oxide and either butyloctyl salicylate or C 12-C15 alkyl benzoates as the carrier had low SPF and UVA-PF values.
- Control sunscreen formulations comprising ethylhexyl methoxycrylene (SOLASTAYTM S i ) and no zinc oxide also had low SPF and UVA-PF values.
- sunscreen formulations comprising dispersions of zinc oxide with ethylhexyl methoxycrylene (SOLASTAY IM S 1 ) as the carrier had significantly higher SPF and UVA-PF values.
- SOLASTAY IM S 1 ethylhexyl methoxycrylene
- Titanium dioxide dispersions using ethylhexyl methoxycrylene (SOLASTAYTM Si), butyloctyl salicylate (control), or C 12- 15 alkyl benzoate (control) as carriers were supplied by either Dynamic Dispersions LLC “DC I” or Kobo Products “Kobo” and formulated as shown in Table 6.
- the titanium dioxide particles were coated with either
- Sunscreens were formulated comprising 7% to 10% of the titanium dioxide dispersions of Table 6 and the SPF and UVA-PF values were determined as shown in Table 7.
- Control sunscreen formulations comprising dispersions of titanium dioxide and either butyloctyl salicylate or C12-C15 alkyl benzoates as the carrier had low SPF and UVA-PF values.
- Control sunscreen formulations comprising ethylhexyl methoxycrylene
- sunscreen formulations comprising dispersions of titanium dioxide with ethylhexyl methoxycrylene (SOLASTAYTM Si) as the carrier had significantly higher SPF and UVA-PF values.
- SOLASTAYTM Si ethylhexyl methoxycrylene
- alkoxycrylene compound of Formula I were compared to zinc oxide dispersions comprising oxycrylene or to zinc oxide dispersions with a high dielectric constant. The synergies of these dispersions were then calculated and are shown in Table 9. Synergy is the magnitude of the SPF or UVA-PF value over the SPF or UVA-PF value that would be expected from purely an additive effect. The purely additive effect results from the addition of, for example, the SPF value of a dispersion comprising alkoxycrylene and no zinc oxide to the SPF value of a dispersion comprising only zinc oxide and no alkoxycrylene. Dispersions comprising the alkoxycrylene compound of Formula I combined with zinc oxide show astonishing +66% and +29% synergies for the SPF and UVA-PF values, respectively.
Abstract
Description
Claims
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JP2012527875A JP2013503863A (en) | 2009-09-04 | 2010-07-02 | Dispersion of inorganic fine particles containing alkoxycrylene |
AU2010290001A AU2010290001B2 (en) | 2009-09-04 | 2010-07-02 | Dispersions of inorganic particulates containing alkoxycrylene |
EP10730335A EP2473237A2 (en) | 2009-09-04 | 2010-07-02 | Dispersions of inorganic particulates containing alkoxycrylene |
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US12/554,329 US8133477B2 (en) | 2007-08-09 | 2009-09-04 | Dispersions of inorganic particulates containing alkoxycrylene |
US12/554,329 | 2009-09-04 |
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EP (1) | EP2473237A2 (en) |
JP (1) | JP2013503863A (en) |
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US20100021403A1 (en) | 2010-01-28 |
AU2010290001A1 (en) | 2012-04-05 |
BRPI1003263A2 (en) | 2012-04-10 |
EP2473237A2 (en) | 2012-07-11 |
US8133477B2 (en) | 2012-03-13 |
AU2010290001B2 (en) | 2016-09-29 |
JP2013503863A (en) | 2013-02-04 |
WO2011028320A3 (en) | 2012-05-31 |
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